A strain of Rhodococcus and use thereof for preparing optical pure chiral sulphoxide

A technology of rhodococcus and pure benzyl sulfoxide, which is applied in the field of rhodococcus and its use in the production of optically pure chiral sulfoxide, can solve the problems of low ee value of the product and difficulty in meeting the purity requirements, and achieve good catalysis effect, ease of preparation, and mild reaction conditions

Inactive Publication Date: 2009-02-25
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these asymmetric oxidations of thioethers using the whole cell as a catalyst generally have low ee values, and it is difficult to meet the purity requirements in the synthesis process.

Method used

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  • A strain of Rhodococcus and use thereof for preparing optical pure chiral sulphoxide
  • A strain of Rhodococcus and use thereof for preparing optical pure chiral sulphoxide
  • A strain of Rhodococcus and use thereof for preparing optical pure chiral sulphoxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 Screening of bacterial strains

[0034] Prepare enriched medium with the following components: (NH 4 ) 2 SO 4 1.0g / L, KH 2 PO 4 3.0g / L, K 2 HPO 4 6.0g / L, MgSO 40.5g / L, CaCl 2 0.05g / L; another rich medium is prepared, the composition is as follows: glucose 15g / L, yeast extract 5g / L, peptone 5g / L, KH 2 PO 4 1.0g / L, K 2 HPO 4 1.0g / L, MgSO 4 0.5g / L, pH7.0. Take a small amount of soil samples and suspend them in 2ml enrichment medium, add sulfide anisole Tween-80 emulsion or methanol solution as the only carbon source, carry out two rounds of enrichment culture under the condition of 25~40℃, the total It takes 2 to 4 days; perform thin-plate chromatography after the enrichment culture, and semi-quantitatively detect the presence or content of the product benzyl sulfoxide. For the enriched culture solution with obvious thioether oxidation products, take a small amount of dilution and spread it on the rich medium plate to cultivate for 1 to 2 days, and ...

Embodiment 2

[0035] Example 2 Culture of microorganisms

[0036] Medium formula: glucose 15g / L, yeast extract 5g / L, peptone 5g / L, KH 2 PO 4 1.0g / L, K 2 HPO 4 1.0g / L, MgSO 4 0.5g / L, pH7.0, high temperature sterilization at 121℃ for 20min.

[0037] Take the Rhodococcus slant preserved at 4°C, pick a ring and inoculate it into a 250ml shake flask containing 50ml of culture medium. Cultivate at 160rpm for 12h at 30°C, transfer to a 500ml shake flask containing 100ml medium at a 5% (v / v) inoculum size, continue to cultivate at 30°C and 160rpm for 30h, and harvest the cells by centrifugation. The measured enzyme activity of the fermentation broth is about 34U / L, the cell concentration is about 30g (wet weight) / L, and the enzyme activity of the unit wet cell is 1.0U / g wet cell.

[0038] The cell enzyme activity unit is defined as the amount of cells required to catalyze the oxidation of thioanisole to produce 1.0 μmol of phenylsulfoxide per minute under the conditions of 30°C and pH 8.0.

Embodiment 3

[0039] Example 3 Preparation of (S)-(-)-Benzyl Sulfoxide Using Resting Cells

[0040] Suspend 12 g of resting cells of Rhodococcus sp. ECU0066 obtained by centrifugation in 100 ml of phosphate buffer (50 mM, pH 8.0), add the substrate sulfide anisole, and make the final concentration 5 mM, and set the temperature at 30 ° C and 160 rpm After shaking and reacting on a constant temperature shaker for 4 hours, the reaction solution was centrifuged at 12,000×g for 10 minutes to remove cells. NaCl was added to the supernatant until saturated, extracted with 50 ml of ethyl acetate, and repeated three times. The cells obtained by centrifugation were soaked with 20 ml of ethyl acetate, repeated twice, the two parts of ethyl acetate were combined, and then washed twice with saturated NaCl solution, 10 ml each time. The obtained ethyl acetate extract was dried overnight with anhydrous sodium sulfate, and the ethyl acetate was removed by rotary evaporation to obtain a crude crystalline p...

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Abstract

The invention discloses a Rhodococcus (Rhodococcus sp.ECU0066) and the use thereof, and the culture collection number of the strain is CGMCC No.2547. The resting cells of the strain is taken as a biological catalyst, and prochiral phenyl alkyl sulfide and a derivative thereof are carried out catalytic oxidation asymmetrically to obtain benzoylate sulfoxide and a derivative thereof with optical activity. The strain and the stereoselective biological oxidation process have the advantages of better catalysis effect, simple and safe operation and low cost, the product is easily purified and is friendly to environment.

Description

technical field [0001] The invention belongs to the field of biochemical industry, and relates to a rhodococcus strain and its application for producing optical pure chiral sulfoxide. technical background [0002] Organosulfur compounds have been widely used in organic synthesis for a long time. Optically active sulfoxides are also increasingly used in asymmetric synthesis as an important tool for inducing many asymmetric transformations. Especially in the past 20 years, the application of chiral sulfoxide compounds as chiral auxiliary reagents in the field of asymmetric synthesis has shown exponential growth, and the role of chiral sulfoxide functional groups in the formation of carbon-carbon bonds and carbon-heterobonds has been established. Status as the most efficient and versatile chiral control factor. [0003] As one of the most successful and effective chiral control factors, chiral sulfoxide compounds have at least three favorable factors: (1) Chiral sulfoxide has...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12N1/20C12P11/00C12R1/01
Inventor 许建和李爱涛张建栋卢文芽林国强
Owner EAST CHINA UNIV OF SCI & TECH
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